Numerous control agents have been proposed for use against diseases of agricultural and horticultural crops. For example, Patent Document 1 discloses a tetrazolyloxime derivative (general formula (P)) that has superior pharmacological efficacy for useful plants, and proposes the use of that derivative as a plant disease control agent.

In general formula (P), A′ represents a halogen atom, alkyl group, alkoxy group, methanesulfonyl group, trifluoromethyl group, aryl group, cyano group or nitro group, n represents an integer of 0 to 5, Y′ represents an alkyl group, and Het represents a substituted pyridyl group or substituted thiazolyl group. Furthermore, in general formula (P), “N˜O” indicates that the aforementioned oxime moiety may be of the (E) form or (Z) form.

The tetrazolyloxime derivative represented by this general formula (P) can be produced by obtaining a tetrazolylhydroxyimino derivative represented by general formula (R) by reacting hydroxylamine with a 1-alkyl-5-benzoyl-1H-tetrazole derivative represented by general formula (Q), and then reacting this with Het-CH2X (wherein, X represents a chlorine atom, bromine atom or iodine atom) in the presence of a base (such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, triethylamine, pyridine or N,N-dimethylaminopyridine). Furthermore, the 1-alkyl-5-benzoyl-1H-tetrazole derivative represented by general formula (Q) can be synthesized by, for example, the method disclosed in Patent Document 2. In addition, a halogenated picoline derivative described in Patent Document 3, for example, can be used for the Het-CH2X.
The tetrazolyloxime derivative represented by general formula (P) has (E) form and (Z) form stereoisomers based on the carbon-nitrogen double bond of the oxime moiety. Although both the (Z) form and (E) form have activity, the (Z) form is preferable.